Copper-catalyzed asymmetric dearomatizing amination of 2-naphthols:Csp^(2)–N coupling via 1,3-reductive elimination  

作　　者：Aying Yihuo Maoping Pu Zheng Tan Jibang Liao Jiuqi Tan Qi-Lin Zhou Xiaohua Liu Xiaoming Feng 

机构地区：[1]Key Laboratory of Green Chemistry&Technology,Ministry of Education,College of Chemistry,Sichuan University,Chengdu 610064,China [2]Key Laboratory and Institute of Elemento-Organic Chemistry,College of Chemistry Frontiers Science Centerfor New Organic Matter,Nankai University,Tianjin300071,China

出　　处：《Science China Chemistry》2024年第8期2694-2700,共7页中国科学（化学英文版）

基　　金：supported by the National Natural Science Foundation of China(22188101);Sichuan Science and Technology Program(2021YJ0561)。

摘　　要：An efficient catalytic asymmetric dearomatizing amination of 2-naphthols and phenols catalyzed by N,N′-dioxide-copper(I)complex as a chiral catalyst was presented.A variety of optically activeβ-naphthalenone compounds with a nitrogen-containing quaternary carbon stereocenter were obtained with high yield and enantioselectivity under mild reaction conditions.Mechanistic studies indicated that this Csp^(2)–N dearomatizing coupling proceeds via 1,3-reductive elimination of phenolate-Cu~Ⅲ-amino intermediate in five-membered ring transition states.The origin of enantioselectivity has also been elucidated based on density functional theory calculations.

关 键 词：asymmetric catalysis AMINATION DEAROMATIZATION copper catalysis coupling reaction 

分 类 号：O621.251[理学—有机化学]